How can you compare downtown Chicago to Madison WI? Seriously. Its not even in the same category. Any downtown of a large city is going to to be completely different than a small podunk town. Lets see population of Madison WI - 220k. Population of Chicago 3 mil (9.7 in chicagoland area).
Naperville is 150k population so its close to Maidson in size and is a fair comparison and why I choose it.
Want to compare Madison with Chicago? How many football teams does Madison have (no, the Badgers don't count)? Baseball? Shopping? Industry? Is it on a great lake? Airport? Museums? Duh...
If you want to compare Chicago to other MAJOR cities I think you will find it very livable, very clean with alot of cultural events. I'd put it up against many other cities 'downtowns' that I have visited.
I've been to nearly every major city in the US and I can tell you Chicago has alot more going for it than most. Try visiting Minneapolis, Houston, Dallas, New Orleans, Detroit, St Louis etc. Most do not have nearly the public transportation system, shopping, nightlife etc that Chicago has. Detroit is a veritable war zone in parts of downtown. Downtown Houston is a ghost town past 6pm. What is the highlight in St Louis? A crummy 600ft arch (just a bit more than half the size of Chicago's two observation decks) and riverboat gambling? Please.
Maybe you are just jealous because you can't afford to live here at least not in a good area. Condo's in downtown Chicago go for 350k and up. Its pricy because people like to live here and there are ALOT of people who live downtown Chicago. If you want to live in Trump's new building on the river its going to set you back 800k and up.
Just because we have trolls living on the South Side of the city that make all the headlines in your local news doesn't mean that all the city is bad.
It sounds to me like you haven't spent a whole lot of time here. I'd suggest you come with some facts or reasons on why you are bashing Chicago vs just another empty opinion. Of course, every other post you have had here has zero substance as well so what should I expect?
Some pictures of our fine city that I personally took. Not sure how you can compare this to Madison but ok.